Alkanediol composition, process for producing the same, and cosmetic

ABSTRACT

A less malodorous alkanediol composition, a process for producing the alkanediol composition efficiently, and a cosmetic containing the alkanediol composition are provided. 
     An alkanediol composition contains 0.005 parts by mass or less of ester compound per 100 parts by mass of alkanediol compound having four or more carbon atoms. An alkanediol composition contains 0.2 parts by mass or less of dioxane compound per 100 parts by mass of alkanediol compound having four or more carbon atoms. Furthermore, an ether-containing dihydric alcohol is preferably 0.3 parts by mass or less per 100 parts by mass of alkanediol compound.

TECHNICAL FIELD

The present invention relates to an alkanediol composition, a processfor producing the alkanediol composition, and a cosmetic, and moreparticularly to an alkanediol composition that contains little specificby-products and that generates no unpleasant smell, a process forproducing the alkanediol composition, and a cosmetic.

BACKGROUND ART

It is unavoidable for manufacturers of organic compounds that organicchemical reactions are associated with the formation of by-products. Theamount of by-product is often much smaller than that of end product.However, even a small amount of by-product sometimes chemically affectsan end product, for example, by worsening the color or smell of the endproduct. For manufacturers of organic compounds, preventing theformation of disadvantageous by-products or finally removingdisadvantageous by-products to prevent these adverse effects is part ofmanufacturing processes.

In such a situation, alkanediol compounds have been used in variousapplications, such as cosmetic preservatives and humectants, pearlingagents, raw materials for synthetic fiber, raw materials for urethanecompounds, and water-based inks. However, particularly in cosmeticapplications, the smell of alkanediol compounds formulated in productscauses a big problem. For example, the addition of an alkanediolcompound to a product free from a perfume impairs the unscented product.Even in a product containing a perfume, the addition of a malodorousalkanediol compound changes the smell of the product. Hence, there hasbeen a great demand for an odorless or less malodorous alkanediolcomposition in cosmetic applications.

A currently common process for producing an alkanediol compositionincludes oxidizing an olefin with an oxidizing agent such as hydrogenperoxide to produce an epoxy compound and hydrolyzing the epoxycompound. Because an alkanediol composition thus produced has a smell,the alkanediol composition is usually purified by distillation, which isa common purification method (see Patent Documents 1 and 2, forexample).

Patent Document 1: Japanese Unexamined Patent Application PublicationNo. 57-62234

Patent Document 2: Japanese Unexamined Patent Application PublicationNo. 60-78928

DISCLOSURE OF INVENTION Problems to be Solved by the Invention

However, as described in Patent Document 1 or 2, alkanediol compositionshave a smell even after distillation. This is because a componentcausing a smell is not identified, and the distillation is performedwithout knowing the component to be removed. Accordingly, it is anobject of the present invention to provide a less malodorous alkanediolcomposition, a process for producing the alkanediol compositionefficiently, and a cosmetic containing the alkanediol composition.

Means for Solving the Problems

As a result of diligent investigations on the above-mentioned problems,the present inventors identified a specific component causing a smell inan alkanediol composition and perfected the present invention bydiscovering that a less malodorous alkanediol composition can beproduced by reducing the specific compound to a certain level.

Thus, an alkanediol composition according to the present inventioncontains 0.005 parts by mass or less of ester compound (A) per 100 partsby mass of alkanediol compound having four or more carbon atoms.

Furthermore, another alkanediol composition according to the presentinvention contains 0.2 parts by mass or less of dioxane compound (C) per100 parts by mass of alkanediol compound having four or more carbonatoms.

Furthermore, in the present invention, an ether-containing dihydricalcohol (B) is preferably 0.3 parts by mass or less per 100 parts bymass of alkanediol compound.

Furthermore, an alkanediol compound having a general formula (1) cansuitably be used in the present invention:

wherein R denotes an alkyl group having 4-15 carbon atoms. Furthermore,the alkanediol compound is preferably a hydrolysate of an epoxy compoundproduced by an oxidation reaction of an olefin.

Furthermore, a process for producing an alkanediol composition accordingto the present invention includes the steps of (a) oxidizing an olefinto produce an epoxy compound, (b) hydrolyzing the epoxy compound toproduce the alkanediol composition, and (c) adding water and/or anorganic solvent to the alkanediol composition and removing water and/orthe organic solvent under reduced pressure.

A cosmetic according to the present invention contains an alkanediolcomposition according to the present invention.

ADVANTAGES OF THE INVENTION

An alkanediol composition according to the present invention has littlesmell. Furthermore, cosmetics containing an alkanediol compositionaccording to the present invention do not have any problem caused by thesmell of the alkanediol composition. An alkanediol compositioncontaining a low concentration of component causing a smell canefficiently be produced by a process for producing an alkanediolcomposition according to the present invention.

BEST MODE FOR CARRYING OUT THE INVENTION

An alkanediol compound that can be used in the present invention has atleast four carbon atoms. In addition, any two hydrogen atoms of asaturated aliphatic hydrocarbon of the alkanediol compound are replacedby hydroxyl groups. Examples of the alkanediol compound include1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol,neopentyl glycol, isoprene glycol (3-methyl-1,3-butanediol),1,2-hexanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol,1,2-octanediol, 2,3-octanediol, 2-ethyl-1,3-hexanediol,2-butyl-2-ethyl-1,3-propanediol, 2,5-dimethyl-2,5-hexanediol,1,2-decanediol, 1,2-dodecanediol, 1,2-tetradecanediol,1,2-hexadecanediol, 1,2-octadecanediol, 1,12-octadecanediol,1,2-cyclohexanediol, 1,4-cyclohexanediol, and 1,4-cyclohexanedimethanol.

Among others, vicinal compounds that have two hydroxyl groups onadjacent carbon atoms are preferred. Compounds having a general formula(1) are more preferred:

wherein R denotes an alkyl group having 4-15 carbon atoms. Examples ofthe alkyl group include a butyl group, an isobutyl group, a secondarybutyl group, a tertiary butyl group, a pentyl group, an isopentyl group,a secondary pentyl group, a neopentyl group, a tertiary pentyl group, ahexyl group, a secondary hexyl group, a heptyl group, a secondary heptylgroup, an octyl group, a secondary octyl group, a nonyl group, asecondary nonyl group, a decyl group, a secondary decyl group, anundecyl group, a secondary undecyl group, a dodecyl group, a secondarydodecyl group, a tridecyl group, an isotridecyl group, a secondarytridecyl group, a tetradecyl group, a secondary tetradecyl group, ahexadecyl group, a secondary hexadecyl group, a stearyl group, a2-ethylhexyl group, a 2-butyloctyl group, a 2-butyldecyl group, and a2-hexyloctyl group.

The alkyl groups preferably have 4-9 carbon atoms, more preferably 4-7carbon atoms, still more preferably 4-6 carbon atoms, and mostpreferably 5 carbon atoms.

While an alkanediol composition according to the present invention maybe produced by any process, the alkanediol composition may be producedby oxidizing an olefin into an epoxy compound and subsequentlyhydrolyzing the epoxy compound. The olefin may be oxidized with anoxidizing agent, such as hydrogen peroxide, a peroxide compound, or aninorganic oxidizing agent. The epoxy compound may be hydrolyzed by adirect reaction with water under high pressure or by a reaction betweenthe epoxy compound and formic acid or acetic acid, followed byhydrolysis with an alkaline substance. Alkanediol compositions thusproduced always contain by-products, such as ester compounds,unsaturated alcohols, or acetal compounds. However, compounds causingsmells have not been identified. Thus, alkanediol compositions areusually purified by distillation, which is a common purification method,as described above. However, smells of the alkanediol compositionscannot be removed by distillation alone.

As a result of investigations, the present inventors found that estercompounds and dioxane compounds have the largest influence on the smellamong compounds causing smells. In an alkanediol composition accordingto a first embodiment of the present invention, therefore, the contentof an ester compound (A) must be 0.005 parts by mass or less per 100parts by mass of alkanediol compound. The term “ester compound (A)”means a compound having an ester bond and includes reaction productsbetween epoxy compounds and fatty acids, such as formic acid and aceticacid, reaction products between alkanediol compounds and fatty acids,and reaction products between compounds having a carbonyl group, whichare produced by the oxidation of olefins, and epoxy compounds oralkanediol compounds. These ester compounds cause a smell. Hence, thecontent of an ester compound in an alkanediol composition according tothe present invention is 0.005 parts by mass or less, preferably 0.003parts by mass or less, and more preferably 0.001 parts by mass or lessper 100 parts by mass of alkanediol compound. More than 0.005 parts bymass of ester compound (A) in an alkanediol composition causes anunpleasant smell.

In an alkanediol composition according to a second embodiment of thepresent invention, the content of a dioxane compound (C) must be 0.2parts by mass or less per 100 parts by mass of alkanediol compound. Inthe present invention, reduction in the amount of dioxane compound (C)can also reduce a smell. Examples of the dioxane compound (C) includecompounds having general formulae (2) and (3) (wherein R is as definedabove). The dioxane compound (C) may be produced by a dehydrationcondensation reaction of alkanediols or a condensation reaction ofunreacted epoxy compounds. The content of the dioxane compound (C) in analkanediol composition according to a second embodiment of the presentinvention is 0.2 parts by mass or less, preferably 0.15 parts by mass orless, and more preferably 0.1 parts by mass or less per 100 parts bymass of alkanediol compound. More than 0.2 parts by mass of dioxanecompound (C) in an alkanediol composition causes an unpleasant smell.

In the present invention, as described above, reduction of the contentof either the ester compound (A) or the dioxane compound (C) leads to aless malodorous alkanediol composition. Another by-product causing asmell of an alkanediol composition is an ether-containing dihydricalcohol. Examples of the ether-containing dihydric alcohol (B) includecompounds having general formulae (4), (5), and (6) (wherein R is asdefined above). The ether-containing dihydric alcohol (B) may beproduced by a dehydration condensation reaction of alkanediols. Thecontent of the ether-containing dihydric alcohol (B) in an alkanediolcomposition according to the present invention is preferably 0.3 partsby mass or less, more preferably 0.2 parts by mass or less, and stillmore preferably 0.15 parts by mass or less per 100 parts by mass ofalkanediol compound. More than 0.3 parts by mass of ether-containingdihydric alcohol (B) in an alkanediol composition causes an unpleasantsmell.

Such a by-product may be analyzed by a method using an analyzer, such asgas chromatography, liquid chromatography, a mass spectrometer, NMR, orIR, or by titration analysis of a saponification value, the degree ofunsaturation, or a hydroxyl value. In terms of microanalysis of aby-product, the by-product may be analyzed preferably by instrumentalanalysis, more preferably by gas chromatography or with a massspectrometer, and still more preferably by gas chromatography. In analkanediol composition according to the present invention, because thepeak area ratio in a gas chromatography chart indicates the mass ratio,the mass ratio of each component can easily be determined.

Gas chromatography analysis may be performed under any condition underwhich a by-product can be separated. Exemplary conditions are asfollows: a gas chromatograph GC-14B (Shimadzu Corporation) with a J & WScientific DB-1 column (100% dimethylpolysiloxane, inner diameter 0.53mm, length 15 m, film thickness 1.5 μm); a 20 ml/min nitrogen carriergas; an FID detector temperature of 320° C.; an air pressure of 50 kPa;a hydrogen pressure of 50 kPa; and a vaporization chamber temperature of320° C. The column may be held at 60° C. for five minutes, be heated to280° C. at 10° C./min, and be held at 280° C. for three minutes. 0.1 μlof sample diluted to 1.5% by weight in ethanol may be injected with amicrosyringe.

Under the conditions described above, a main peak of 1,2-octanediolappears at a retention time of about 10 min. A peak of a by-product, ifany, appears before or after the main peak. The peak area ratioindicates the mass ratio of each component. A peak of an ester compoundappears zero to two minutes before the retention time of the main peak.A peak of a dioxane compound appears four to seven minutes after theretention time of the main peak. A peak of an ether-containing dihydricalcohol appears eight to fifteen minutes after the retention time of themain peak.

In an alkanediol composition according to a first embodiment of thepresent invention, the peak area of an ester compound appearing zero totwo minutes before the retention time of the main peak must be 0.005% orless, preferably 0.003% or less, and more preferably 0.001% or less ofthe main peak area. When the peak area of an ester compound exceeds0.005% of the main peak area, the content of the ester compound exceeds0.005 parts by mass per 100 parts by mass of alkanediol compound. Acomponent causing a smell and having an unknown structure may appearzero to two minutes after the retention time of the main peak. A peak inthis area is therefore indicative of a strong smell and is notpreferred.

In an alkanediol composition according to a second embodiment of thepresent invention, the peak area of a dioxane compound appearing four toseven minutes after the retention time of the main peak must be 0.2% orless, preferably 0.15% or less, and more preferably 0.1% or less of themain peak area. When the peak area of a dioxane compound exceeds 0.2% ofthe main peak area, the content of the dioxane compound exceeds 0.2parts by mass per 100 parts by mass of alkanediol compound.

The peak area of an ether-containing dihydric alcohol appearing eight tofifteen minutes after the retention time of the main peak is preferably0.3% or less, more preferably 0.2% or less, and still more preferably0.15% or less of the peak area of the main peak. When the peak area ofan ether-containing dihydric alcohol exceeds 0.3% of the main peak area,the content of the ether-containing dihydric alcohol exceeds 0.3 partsby mass per 100 parts by mass of alkanediol compound. This may cause asmell.

An alkanediol composition according to the present invention may beproduced by any known method that can reduce an ester compoundby-product to 0.005 parts by mass or less, and/or that can reduce adioxane compound by-product to 0.2 parts by mass or less, per 100 partsby mass of alkanediol compound. As described above, the content of estercompound and/or the content of dioxane compound cannot be reduced to therange described above by common distillation alone. A smell thereforecannot be removed. This is probably because the boiling points of thecomponents causing a smell, that is, an ester compound and a dioxanecompound, are very close to the boiling point of the alkanediolcompound.

Examples of a purification method used in the production of analkanediol composition according to the present invention includeazeotropic distillation of by-products and a large amount of water underreduced pressure; azeotropic distillation of by-products and an organicsolvent under reduced pressure; azeotropic distillation of by-products,water, and an organic solvent under reduced pressure; blowing of watervapor under reduced pressure; adsorption of by-products on an adsorbent,such as an ion exchange resin or activated carbon, and subsequentdistillation; recrystallization in a solvent, such as ethanol, acetone,or hexane; and combinations thereof; and combinations of these methodsand known purification methods.

Among others, blowing of water vapor under reduced pressure; azeotropicdistillation of by-products and water and/or an organic solvent underreduced pressure (this is a method according to the present invention);and the addition of an organic solvent and blowing of water vapor underreduced pressure are preferred, because an ester compound causing asmell can efficiently be removed by these methods.

In the blowing of water vapor, the total amount of water is preferablyin the range of 30 to 200 parts by mass, more preferably in the range of50 to 150 parts by mass, and still more preferably in the range of 50 to100 parts by mass per 100 parts by mass of alkanediol composition. Thedistillation temperature is preferably in the range of 80° C. to 120°C., more preferably in the range of 85° C. to 110° C., and still morepreferably in the range of 90° C. to 100° C. The degree of vacuum ispreferably 10 kPa or less, more preferably 5 kPa or less, and still morepreferably 1.3 kPa or less.

The amount of the organic solvent is preferably in the range of 30 to200 parts by mass, more preferably in the range of 50 to 150 parts bymass, and still more preferably in the range of 80 to 120 parts by massper 100 parts by mass of alkanediol composition. Furthermore, theorganic solvent may be added in a plurality of portions. For example,the addition and removal of 10 parts by mass of organic solvent may berepeatedly performed. In the addition of the organic solvent in aplurality of portions, the total amount of the organic solvent ispreferably in the range as described above.

The amount of water is preferably in the range of 30 to 200 parts bymass, more preferably in the range of 50 to 150 parts by mass, and stillmore preferably in the range of 80 to 120 parts by mass per 100 parts bymass of alkanediol composition. Furthermore, water may be added in aplurality of portions. For example, the addition and removal of 10 partsby mass of water may be repeatedly performed. In the addition of waterin a plurality of portions, the total amount of water is preferably inthe range as described above. The degree of vacuum is preferably 10 kPaor less, more preferably 5 kPa or less, and still more preferably 1.3kPa or less.

When an organic solvent and water, or an organic solvent and watervapor, are combined, preferably 20-150 parts by mass, more preferably30-100 parts by mass of water or water vapor per 100 parts by mass oforganic solvent is added or blown. The total amount of the organicsolvent and water or the total amount of the organic solvent and watervapor is preferably in the range of 50 to 300 parts by mass, morepreferably in the range of 80 to 250 parts by mass, and still morepreferably in the range of 100 to 200 parts by mass per 100 parts bymass of alkanediol composition. The degree of vacuum is preferably 10kPa or less, more preferably 5 kPa or less, and still more preferably1.3 kPa or less.

Examples of organic solvent for use in the purification method includeglycol compounds, such as ethylene glycol, propylene glycol, butyleneglycol, diethylene glycol, dipropylene glycol, methyl cellosolve, ethylcellosolve, propyl cellosolve, butyl cellosolve, propylene glycolmonomethyl ether, and diethylene glycol monomethyl ether; acyclichydrocarbons, such as hexane, octane, nonane, and decane; and aromatichydrocarbons, such as benzene, toluene, xylene, trimethylbenzene,cumene, and naphthalene. Among others, in terms of removal ofby-products, glycol solvents are preferred, propylene glycol,dipropylene glycol, and diethylene glycol are more preferred, andpropylene glycol is most preferred.

If necessary, another component may be added to an alkanediolcomposition according to the present invention within the limits notcompromising the advantages of the present invention. Examples of theadditive component include water; surfactants, such as nonionicsurfactants, anionic surfactants, cationic surfactants, and amphotericsurfactants; antioxidants; light stabilizers; silicone oils; thickeners;oil solutions; powders (pigments, dyes, and resins); preservatives;perfumes; humectants; bioactive components; salts; solvents;antioxidants; chelating agents; counteractives; pH adjusters; enzymes;and cyclic oligosaccharides such as cyclodextrins.

An alkanediol composition according to the present invention may beallowed to react with another compound reactive with a hydroxyl group.Examples of the compound reactive with a hydroxyl group includeisocyanate compounds, epoxy compounds, and compounds containingcarboxylic acids such as fatty acids. An alkanediol compositionaccording to the present invention may be allowed to react with thesecompounds and thereby be included in urethane resins, epoxy resins, andpolyesters. Furthermore, because an alkanediol composition according tothe present invention contains only a small amount of by-products, fewside reactions occur, and a final product advantageously contains only asmall amount of by-products.

A cosmetic according to the present invention contains an alkanediolcomposition according to the present invention. In the cosmetic, thealkanediol composition may be used as a humectant or a preservative, ora pearling agent in a shampoo. Examples of the cosmetic include facialcleansing creams, cleansing foams, cleansing creams, cleansing milks,cleansing lotions, massage creams, cold creams, moisture creams, sunblocks, body shampoos, hair shampoos, hair rinses, hair treatments,hair-restorers, hair creams, hair lacquers, setting lotions, hairbleaches, color rinses, permanent wave lotions, hand creams, lipsticks,packs, foundations, toilet water, cosmetic liquid, milky lotions,colognes, bath cosmetics, kitchen detergents, laundry detergents, bathdetergents, nail cosmetics, and tooth powders.

EXAMPLES

The present invention will be further illustrated with examples below.

Production of Diol Compound Production Example 1 Production ofOctanediol

381 g (3.4 mol) of α-olefin having eight carbon atoms and 218 g (4.5mol) of 95% formic acid were charged into a 2000 ml four-neck glassflask with a stirrer, a thermometer, and a nitrogen inlet. Then, 261 g(4.6 mol) of 60% hydrogen peroxide was added dropwise at 60° C. for twohours. After the completion of dropping, the reactant was aged at 60° C.for eight hours. After the reactant was left to stand and a loweraqueous layer was removed, 192 g (1.2 mol) of 25% aqueous sodiumhydroxide was added to the reactant. The reactant was stirred at 60° C.for 30 minutes for saponification and was left to stand. A lower aqueouslayer was then removed. After the saponification and removal of theaqueous layer were performed one more time, the product was washed withhot water and hexane to yield 380 g of 1,2-octanediol.

Production Example 2 Production of Decanediol

As in Production Example 1, 1,2-decanediol was produced from an α-olefinhaving 10 carbon atoms.

Production Example 3 Production of Dodecanediol

As in Production Example 1, 1,2-dodecanediol was produced from anα-olefin having 12 carbon atoms.

Purification Treatment 1

A hundred grams of diol compound produced in Production Example 1, 2, or3 and 100 g of propylene glycol were charged into a 500 ml four-neckglass flask with a stirrer, a thermometer, and a nitrogen inlet. Thereactant was heated to 90° C. to 95° C. Propylene glycol was thencompletely removed at a reduced pressure of 1.33 kPa to yield a purifieddiol compound.

Treatment 2

A hundred grams of diol compound produced in Production Example 1, 2, or3, 100 g of propylene glycol, and 50 g of water were charged into a 500ml four-neck glass flask with a stirrer, a thermometer, and a nitrogeninlet. The reactant was heated to 90° C. to 95° C. Propylene glycol wasthen completely removed at a reduced pressure of 1.33 kPa to yield apurified diol compound.

Treatment 3

A hundred grams of diol compound produced in Production Example 1, 2, or3 was charged into a 300 ml four-neck glass flask with a stirrer, athermometer, and a nitrogen inlet. The reactant was distilled at atemperature in the range of 120° C. to 180° C. and a reduced pressure inthe range of 1.4 to 1.8 kPa to yield a purified diol compound as a mainfraction.

Treatment 4

Fifty grams of diol compound produced in Production Example 1, 2, or 3and 10 g of activated carbon were charged into a 200 ml beaker and werestirred at 50° C. After two hours, the activated carbon was filtered outto yield a purified diol compound.

The purified diol compounds thus produced were analyzed by gaschromatography under conditions described below. Peak areas werecalculated to determine the amounts of impurities. The amounts ofimpurities were expressed as ratios of peak area to that of the mainpeak (diol compound), which was set to be 100. Tables 1 to 3 show theresults for 1,2-octanediol (Production Example 1), 1,2-decanediol(Production Example 2), and 1,2-dodecanediol (Production Example 3),respectively.

Analyzer: GC-14B (Shimadzu Corporation)

Column: DB-1 (J & W Scientific, 100% dimethylpolysiloxane, innerdiameter 0.53 mm, length 15 m, film thickness 1.5 μm)

Carrier gas: Nitrogen, 20 ml/min

Air pressure: 50 kPa

Hydrogen pressure: 50 kPa

Temperature of vaporization chamber: 320° C.

Heating rate: held at 60° C. for five minutes, heated to 280° C. at 10°C./min, and held at 280° C. for three minutes.

Sample amount: 0.1 μl (1.5% by weight in ethanol)

TABLE 1 Retention time (min) 8.3~10.2 10.3 10.4~12.3 14.3~17.3 18.3~25.3Treatment 1 0.003 100 0 0.16 0.29 Treatment 2 0.001 100 0 0.03 0.25Treatment 3 0.03 100 0 0.29 0.41 Treatment 4 0.13 100 0 0.32 0.48Untreated 0.25 100 0.05 0.48 0.58 Identified Ester Diol — Dioxane Ether-components compound compound compound containing dihydric alcohol

TABLE 2 Retention time (min) 11.1~13.0 13.1 13.2~15.1 17.1~20.121.1~28.1 Treatment 1 0.006 100 0 0.18 0.32 Treatment 2 0.002 100 0 0.040.23 Treatment 3 0.05 100 0 0.30 0.42 Treatment 4 0.14 100 0 0.33 0.51Untreated 0.23 100 0.04 0.46 0.61 Identified Ester Diol — Dioxane Ether-components compound compound compound containing dihydric alcohol

TABLE 3 Retention time (min) 13.7~15.6 15.7 15.8~17.7 19.7~22.723.7~30.7 Treatment 1 0.006 100 0 0.19 0.29 Treatment 2 0.002 100 0 0.060.21 Treatment 3 0.05 100 0 0.25 0.41 Treatment 4 0.15 100 0 0.32 0.49Untreated 0.21 100 0.03 0.45 0.6 Identified Ester Diol — Dioxane Ether-components compound compound compound containing dihydric alcohol

Test Example 1

Alkanediol compounds in Treatments 1 to 4 and untreated alkanediolcompounds were evaluated by ten panelists (five men and five women) forevaluation items described below. Table 4 shows the results.

◯: No smell.

Δ: A little smell but not unpleasant.

x: Unpleasant smell.

TABLE 4 Number of Panelists ∘ Δ x Treatment 1 1,2-octanediol 9 1 01,2-decanediol 8 2 0 1,2-dodecanediol 9 1 0 Treatment 2 1,2-octanediol10 0 0 1,2-decanediol 10 0 0 1,2-dodecanediol 10 0 0 Treatment 31,2-octanediol 0 4 6 1,2-decanediol 0 3 7 1,2-dodecanediol 0 4 6Treatment 4 1,2-octanediol 0 2 8 1,2-decanediol 0 1 9 1,2-dodecanediol 01 9 Untreated 1,2-octanediol 0 0 10 1,2-decanediol 0 0 101,2-dodecanediol 0 0 10

These results show that, in gas chromatography, a large peak (estercompound) at zero to two minutes before the peak of a diol compoundand/or a large peak (dioxane compound) at four to seven minutes afterthe peak of the diol compound are indicative of an unpleasant smell.

Test Example 2

1,2-octanediol in Production Example 1 was purified by the methoddescribed in Treatment 2. Shampoos were prepared with the purified1,2-octanediol and untreated 1,2-octanediol according to the formulashown in Table 5. The two shampoos were evaluated by ten panelists (fivemen and five women) for smell when the shampoos were used.

TABLE 5 Amount Component (% by mass) Sodium polyoxyethylene (3) laurylether sulfate 25.0 Lauryl amine oxide 3.0 Lauryl amine propyl betaine18.0 Propylene glycol 3.2 Hydroxyethyl cellulose 0.5 1,2-octanediol 0.1Purified water Remainder

As a result of evaluating the smell of shampoo, nine panelists felt thatthe smell of the shampoo containing a 1,2-octanediol compositionpurified by the method described in Treatment 2 was better than that ofthe shampoo containing an untreated 1,2-octanediol composition; onepanelist felt that the two shampoos have the same smell; and no panelistfelt that the smell of the shampoo containing an untreated1,2-octanediol composition was better than that of the shampoocontaining a purified 1,2-octanediol composition.

1. An alkanediol composition comprising 0.005 parts by mass or less of ester compound (A) per 100 parts by mass of alkanediol compound having four or more carbon atoms.
 2. An alkanediol composition comprising 0.2 parts by mass or less of dioxane compound (C) per 100 parts by mass of alkanediol compound having four or more carbon atoms.
 3. The alkanediol composition according to claim 1, further comprising 0.3 parts by mass or less of ether-containing dihydric alcohol (B) per 100 parts by mass of the alkanediol compound.
 4. The alkanediol composition according to claim 1, wherein the alkanediol compound has a general formula (1):

wherein R denotes an alkyl group having 4-15 carbon atoms.
 5. The alkanediol composition according to claim 1, wherein the alkanediol compound is a hydrolysate of an epoxy compound produced by an oxidation reaction of an olefin.
 6. A process for producing an alkanediol composition, comprising the steps of: (a) oxidizing an olefin to produce an epoxy compound; (b) hydrolyzing the epoxy compound to produce the alkanediol composition; and (c) adding water and/or an organic solvent to the alkanediol composition and removing water and/or the organic solvent under reduced pressure.
 7. A cosmetic comprising the alkanediol composition according to claim
 1. 